Tom Brady didn’t know when to fold ’em. So what?

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This week, one day before Groundhog Day, Tampa Bay quarterback Tom Brady retired. Yes, again.

The superstar first announced his retirement last year, earning a blitz of kudos. And then, 40 days later, Mr. Brady revealed that he had changed his mind. He was 44 – very old in football years – but even after setting all those records over more than two decades in the NFL, there was unfinished business.

And then, the GOAT stumbled. He had a lacklustre (for him) season – his only losing season as an NFL starter. And he had an even lousier year, personally: He and his wife, supermodel Gisele Bundchen, publicly split. There were reports that his refusal to leave pro football was a contributing factor.

Now, he’s retiring “for good,” he said. “I know the process was a pretty big deal last time, so when I woke up this morning I figured I’d just press record and let you guys know first,” he said on a self-shot smartphone video, on a cloudy, windy beach.

On Twitter, people responded with snarky “see you next year” messages and posted predictive rise-from-the-dead memes.

Even – especially – for someone like Mr. Brady, it is hard to know when to fold ‘em, with apologies to Kenny Rogers. Mr. Brady decided he wasn’t done. It was a gamble, and it didn’t exactly pay off.

Identifying the right time to walk away is tricky, even for us mere mortals. When do we leave that job that has been so good for us? The one we know inside-out, where our colleagues have become like family, where we can sail through another quarter, that’s like a second home?

When do we leave the apartment we’ve outgrown? The city that’s draining our bank account? The boyfriend we know in our gut isn’t really right? Inertia can be powerful.

Athletes typically have their bodies – and their stat sheets – to tell them when it’s time. And politicians have their electorates – but not always. In New Zealand, Jacinda Ardern shocked the world when she announced last month that she was stepping down as prime minister. She was done, she said. Burned out. While many cheered her honesty and courage in making a decision that was best for her life, it was a shame to lose a smart, thoughtful, compassionate prime minister who had led her country with humanity and strength through terrible times.

Closer to home, there are other politicians who may have similar decisions to make about their futures soon, including Justin Trudeau, who has been Prime Minister for almost eight years. Stick around or step down: what’s the best way to be a team player? Is there a risk of being pushed out? Long walks in the snow may ensue.

There are some obvious candidates for stepping away from politics; I can think of one former U.S. president, for instance. And there are some we could really use back in the ring – Naheed Nenshi, are you listening?

It’s easy to mock Tom Brady for retiring, returning and leaving again exactly 365 days later.

But why mock the greatest of all time for wanting to give it another shot, for persevering? Maybe we should applaud that.

Anyway, he’s laughing all the way to the beach, the broadcast booth and, as soon as he’s eligible, the Hall of Fame. He can go anywhere else he wants to be. (With the exception, that is, of Ms. Bundchen’s arms; she is, according to People, “sincerely happy” for him, but has moved on.

Perhaps not coincidentally, the movie 80 for Brady is out this weekend. In the film, four seniors dealing with health issues, aging bodies and widowhood (played by Sally Field, Jane Fonda, Lily Tomlin and Rita Moreno) decide to travel to the 2017 Super Bowl to see Mr. Brady, their hero, play. The four stars are aged 76 to 91 in real life.

I cannot recommend this film. But at the packed prerelease screening I attended, people showed up in Mr. Brady’s #12 jerseys, took photos, and laughed at (some of) the jokes. As bad as the film was, it gave them pleasure.

I thought: how many fans were able to see Mr. Brady play because he decided to stay on an extra year? And how many viewers have gotten similar joy in recent years from these actors who kept going, pushing back against Hollywood’s notorious ageism?

Granted, the four of them probably should have kept on going, past this script. But it’s hard to know when to walk away, when to run. (They should have run.) Mr. Brady miscalculated. But he got another year, as did his fans. Even if it was a miscalculation, for many people, it was good. Maybe that’s what Kenny Rogers meant when he sang about playing the game right.